# HPTP

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Monoaminergic neurotoxin

Pharmaceutical compound

HPTP Clinical data Drug class Serotonergic and dopaminergic neurotoxin Identifiers IUPAC name 4-[4-(4-chlorophenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(4-fluorophenyl)butan-1-one CAS Number 52669-92-8 PubChem CID 171187 ChemSpider 149659 ChEBI CHEBI:177523 ChEMBL ChEMBL3544895 CompTox Dashboard (EPA) DTXSID80200642 Chemical and physical data Formula C21H21ClFNO Molar mass 357.85 g·mol−1 3D model (JSmol) Interactive image SMILES C1CN(CC=C1C2=CC=C(C=C2)Cl)CCCC(=O)C3=CC=C(C=C3)F InChI InChI=1S/C21H21ClFNO/c22-19-7-3-16(4-8-19)17-11-14-24(15-12-17)13-1-2-21(25)18-5-9-20(23)10-6-18/h3-11H,1-2,12-15H2 Key:ZNOLNAPJKOYTHY-UHFFFAOYSA-N

**HPTP** is a [monoaminergic neurotoxin](/source/Monoaminergic_neurotoxin) related to [MPTP](/source/MPTP).[1][2][3][4] It is the [dehydration](/source/Dehydration_reaction) [product](/source/Product_(chemistry)) of [haloperidol](/source/Haloperidol).[1][2][4] The agent is specifically a [dopaminergic](/source/Dopaminergic_neurotoxin) and [serotonergic neurotoxin](/source/Serotonergic_neurotoxin).[1] HPTP is a [prodrug](/source/Prodrug) of [HPP+](/source/HPP%2B), which mediates its monoaminergic neurotoxicity.[1][2][4] This is analogous to how [MPP+](/source/MPP%2B) mediates the neurotoxicity of MPTP.[1][2][4] Other related compounds include [RHPTP](https://en.wikipedia.org/w/index.php?title=RHPTP&action=edit&redlink=1) and [RHPP+](https://en.wikipedia.org/w/index.php?title=RHPP%2B&action=edit&redlink=1).[5]

## References

1. ^ [***a***](#cite_ref-Kostrzewa2022_1-0) [***b***](#cite_ref-Kostrzewa2022_1-1) [***c***](#cite_ref-Kostrzewa2022_1-2) [***d***](#cite_ref-Kostrzewa2022_1-3) [***e***](#cite_ref-Kostrzewa2022_1-4) Kostrzewa RM (2022). "Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons". *Handbook of Neurotoxicity*. Cham: Springer International Publishing. pp. 159–198. [doi](/source/Doi_(identifier)):[10.1007/978-3-031-15080-7_53](https://doi.org/10.1007%2F978-3-031-15080-7_53). [ISBN](/source/ISBN_(identifier)) [978-3-031-15079-1](https://en.wikipedia.org/wiki/Special:BookSources/978-3-031-15079-1).

1. ^ [***a***](#cite_ref-Igarashi1998_2-0) [***b***](#cite_ref-Igarashi1998_2-1) [***c***](#cite_ref-Igarashi1998_2-2) [***d***](#cite_ref-Igarashi1998_2-3) Igarashi, Kazuo (1998). "The Possible Role of an Active Metabolite Derived from the Neuroleptic Agent Haloperidol in Drug-Induced Parkinsonism". *Journal of Toxicology: Toxin Reviews*. **17** (1): 27–38. [doi](/source/Doi_(identifier)):[10.3109/15569549809006488](https://doi.org/10.3109%2F15569549809006488). [ISSN](/source/ISSN_(identifier)) [0731-3837](https://search.worldcat.org/issn/0731-3837).

1. **[^](#cite_ref-GórskaMarszałłSloderbach2015_3-0)** Górska A, Marszałł M, Sloderbach A (October 2015). "[The neurotoxicity of pyridinium metabolites of haloperidol]" [The neurotoxicity of pyridinium metabolites of haloperidol]. *Postepy Higieny I Medycyny Doswiadczalnej* (in Polish). **69**: 1169–1175. [doi](/source/Doi_(identifier)):[10.5604/17322693.1175009](https://doi.org/10.5604%2F17322693.1175009) (inactive 12 July 2025). [PMID](/source/PMID_(identifier)) [26561842](https://pubmed.ncbi.nlm.nih.gov/26561842).{{[cite journal](https://en.wikipedia.org/wiki/Template:Cite_journal)}}: CS1 maint: DOI inactive as of July 2025 ([link](https://en.wikipedia.org/wiki/Category:CS1_maint:_DOI_inactive_as_of_July_2025))

1. ^ [***a***](#cite_ref-CastagnoliCastagnoliVanderSchyf1999_4-0) [***b***](#cite_ref-CastagnoliCastagnoliVanderSchyf1999_4-1) [***c***](#cite_ref-CastagnoliCastagnoliVanderSchyf1999_4-2) [***d***](#cite_ref-CastagnoliCastagnoliVanderSchyf1999_4-3) Castagnoli N, Castagnoli KP, Van der Schyf CJ, Usuki E, Igarashi K, Steyn SJ, Riker RR (1999). "Enzyme-catalyzed bioactivation of cyclic tertiary amines to form potential neurotoxins". *Pol J Pharmacol*. **51** (1): 31–38. [PMID](/source/PMID_(identifier)) [10389142](https://pubmed.ncbi.nlm.nih.gov/10389142).

1. **[^](#cite_ref-AventDeVossGillam2006_5-0)** Avent KM, DeVoss JJ, Gillam EM (July 2006). "Cytochrome P450-mediated metabolism of haloperidol and reduced haloperidol to pyridinium metabolites". *Chem Res Toxicol*. **19** (7): 914–920. [doi](/source/Doi_(identifier)):[10.1021/tx0600090](https://doi.org/10.1021%2Ftx0600090). [PMID](/source/PMID_(identifier)) [16841959](https://pubmed.ncbi.nlm.nih.gov/16841959).

v t e Monoaminergic neurotoxins Dopaminergic 2′-CH3-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g., disulfiram, methylmercury) Amphetamine V-61 Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP+ HPTP Imidazole propionate (ImP) Mancozeb Maneb Mephedrone Methamphetamine Methcathinone Methylone MPP+ (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol TaClo (1-TCMTC) Ziram Noradrenergic 2′-NH2-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine V-61 Serotonergic 2′-NH2-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA pCPE 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP+ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI Unsorted 2,5-DDM-DOM 5-HIAL RHPP+ RHPTP See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators

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Adapted from the Wikipedia article [HPTP](https://en.wikipedia.org/wiki/HPTP) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/HPTP?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.